Reagent-controlled stereoselective iodolactonizations

被引：115

作者：

Haas, J

Piguel, S

Wirth, T

机构：

[1] Univ Wales Coll Cardiff, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

[2] Univ Basel, Inst Organ Chem, CH-4056 Basel, Switzerland

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 02期

关键词：

D O I：

10.1021/ol0171113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS Iodocyclizations are important transformations and among stereocontrolled iodocyclizations mostly substrate-controlled versions using a chiral auxiliary have been successfully investigated. This work reports on stereoselective reagent controlled iodolactonizations applying a new method using a combination of ICI and a primary amine leading to the highest selectivities known so far.

引用

页码：297 / 300

页数：4

共 29 条

[1] SYNTHESIS OF BOTH ENANTIOMERS OF OPTICALLY PURE SATURATED AND ALPHA,BETA-UNSATURATED GAMMA-SUBSTITUTED GAMMA-LACTONES FROM CHIRAL SULFOXIDES - X-RAY MOLECULAR-STRUCTURE OF (3R,4S)-4-METHYL-4-TERT-BUTYL-3-(PARA-TOLYLTHIO)BUTANOLIDE AND OF (3R,4R)-4-(CYCLOHEX-1-ENYL)-4-METHYL-3-(PARA-TOLYLTHIO)BUTANOLIDEL
ALBINATI, A
BRAVO, P
GANAZZOLI, F
RESNATI, G
VIANI, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08): : 1405 - 1415
[2] ELECTROPHILIC LACTONIZATION AS A TOOL IN ACYCLIC STEREOCONTROL - SYNTHESIS OF SERRICORNIN
BARTLETT, PA
RICHARDSON, DP
MYERSON, J
[J]. TETRAHEDRON, 1984, 40 (12) : 2317 - 2327
[3] BOUGAULT MJ, 1908, ANN CHIM PHYS, V14, P145
[4] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES
CARDILLO, G
ORENA, M
[J]. TETRAHEDRON, 1990, 46 (10) : 3321 - 3408
[5] SYNTHESIS OF THE POLYETHER ANTIBIOTIC MONENSIN .3. COUPLING OF PRECURSORS AND TRANSFORMATION TO MONENSIN
COLLUM, DB
MCDONALD, JH
STILL, WC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) : 2120 - 2121
[6] Mechanistic evaluation of the halocyclization of 4-penten-1-ol by some bis(2-substituted pyridine) and bis(2,6-disubstituted pyridine)bromonium triflates
Cui, XL
Brown, RS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) : 5653 - 5658
[7] De la Mare P. B., 1976, ELECTROPHILIC HALOGE
[8] DOWLE MD, 1979, CHEM SOC REV, P171
[9] FITTIG R, 1904, LIEBIGS ANN CHEM, V331, P142
[10] 1-azatriene cyclisation as a route to annelated pyrido[4,3-b]indoles
Gilchrist, TL
Kemmitt, PD
Germain, AL
[J]. TETRAHEDRON, 1997, 53 (12) : 4447 - 4456

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